Steroidal compounds and methods for obtaining the same



saturated 20 keto pregnane series comp l H: CHr -OHa was added asolution 01 1.3 g. chromic aznhydride I acetylated product crystalliudirom meti'ieiiol to cats as nJfi. 2. 123-1819; yield 0.8 g.

" Patented July 31, 1945 v w 4 UNITED STATES PATENT oFFIc-E;

Romeo B. Wagner, State College, Pa, assisnor to l'arkanavis & Company,Detroit, Mich, a corporation ol Michlta No Drawing. Application May 15,194 Serial No. 532,752

4 Claims. (01. zed-391.4)

This invention relates to the preparation of While the oxidizing agentdescribed, chromic new compounds of the vpregnene series. These acid inacetic acid at room temperature, is the compounds are useiulintermediates in the prepapreferred agent for carrying out this stepother ration of hormone products. agents capable of rupturing acarbon-carbon v In the copending Patent No. 2,352,052, issued 5 doublebond may also be used for example ozone,- July 4, 1944, a method wasdescribed by which per-acids and their salts and the like. a steroidalsapogenins may be isomerized to pseudo- The above describedtransformations may be sapogenins and these pseudo-sapogenins furtherillustrated as follows: mildly'oxldized and hydrolyzed to give 16-1! un-The transformations may be indicated as follows;

.03. 0 on} om tn-tm-onr-tn 0H: omen cm arccn -cm -rr o----c V Y m Mom-o20 1 shows a 7 iorssveralhours g Y cm omen,

OH: OH: ===O H-CHs [gamma H eaten Bo M if" cm 0 I Pseudo magenlntrisgiam e. s. triaoetate) where 3 11195165611125 the rings A, B and C ofthe 5 u e: oglvilagghggugoaggalgatgaexgctmfifigg steroid 11 eus and R isan acyi radical (R20 1 r mm m than representing an acyl anhydride). "9mm I have now found. that these reactions may g CH: $180 be applied tothe newly discoveredsteroidal CH, 4 (311 5:0 Hydgoiy'gig 1 pflseninsyuccazenin and lilasenin which are 0 2908100110110 KOH, described in mpendins pp ication. seri I thenetherex tracflon No. 535,748, filed May15, 1944. The correspondand crystallization in; pseudosenin is'describedin my-popendins application, Serial No. 535,753, filed May 15, 1944. r'45 Since yuccasenin and lilaaenin are isomeric, 7 M0 diflerins only inthe configuration of the' side 5,16- r en-2, moi-2e g 33 y? ggg gggggstrategists To a solution 01! 3. g. of the 'triacetate oipseudoyuccasenin in 150 cc. of glacial acetic acid at 25 in 15 cc. oi80%acetic acid durlna ten minutes. The reaction mixture was worked up asdescribed ,ior the oxidation or pseudohecogeninamjrhe Found: 6.7251;8,8.4. 1W I What IClim is:

1. A cbmpound of the formula L 5 and groups hydrolyzable .to

where Y is a. member of the class consisting of

